US4491585A - Combating pests with novel phenoxypyridylmethyl esters - Google Patents

Combating pests with novel phenoxypyridylmethyl esters Download PDF

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US4491585A
US4491585A US06/355,044 US35504482A US4491585A US 4491585 A US4491585 A US 4491585A US 35504482 A US35504482 A US 35504482A US 4491585 A US4491585 A US 4491585A
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chlorine
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Rainer Fuchs
Ingeborg Hammann
Bernhard Homeyer
Wilhelm Stendel
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Bayer AG
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Bayer AG
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Assigned to BAYER AKTIENGESELLSCHAFT, A CORP. OF GERMANY reassignment BAYER AKTIENGESELLSCHAFT, A CORP. OF GERMANY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: FUCHS, RAINER, HAMMANN, INGEBORG, HOMEYER, BERNHARD, STENDEL, WILHELM
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/647—One oxygen atom attached in position 2 or 6 and having in the molecule an acyl radical containing a saturated three-membered ring, e.g. chrysanthemumic acid esters

Definitions

  • the present invention now provides, as new compounds, the phenoxypyridylmethyl esters of the general formula ##STR5## wherein R represents a radical of the general formula ##STR6## wherein R 4 represents a hydrogen, chlorine or bromine atom, a cyano group or an optionally halogen-substituted alkyl group and
  • R also represents a radical of the general formula ##STR7## wherein R 6 represents an isopropyl or cyclopropyl group and
  • R 1 represents a hydrogen atom, or a cyano, alkyl, alkenyl, or alkinyl group; the alkyl, alkenyl and alkinyl groups containing up to 4 carbon atoms and optionally being substituted by halogen, and
  • the general formula (I) includes the various possible stereoisomers and optical isomers, as well as mixtures thereof.
  • R has the meaning given above, or a reactive derivative thereof, is reacted with a phenoxypyridyl alcohol of the general formula ##STR8## wherein R 1 , R 2 and R 3 have the meanings given above, or with a reactive derivative thereof, if appropriate in the presence of an acid acceptor, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent.
  • the new phenoxypyridylmethyl esters of the present invention are distinguished by a high pesticidal, particularly insecticidal and acaricidal, activity.
  • R 5 represents a hydrogen, chlorine, or bromine atom or an optionally fluorine-substituted and/or chlorine-substituted C 1 to C 4 alkyl or C 1 to C 4 alkoxy group, or
  • R 7 represents a hydrogen or fluorine atom or a trifluoromethyl or chloro-(di)fluoromethyl group
  • R represents a radical of the general formula ##STR11## wherein R 4 represents a chlorine atom and
  • R also represents a radical of the general formula ##STR12## wherein R 6 represents an isopropyl group and
  • R 7 represents a fluorine atom
  • Preferred phenoxypyridinecarbaldehydes of formula (IV) to be used as the starting materials in reaction variant (b) according to the present invention are those in which R 2 and R 3 have the meanings given in the definition of the preferred and particularly preferred compounds of the present invention.
  • diluents in all reaction variants.
  • suitable diluents include, in particular, aliphatic and aromatic, optionally halogenated hydrocarbons (such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon terachloride, chlorobenzene and o-dichlorobenzene), ethers (such as diethyl ether, dibutyl ether, glycol dimethyl ether, diglycol dimethyl ether, tetrahydrofuran and dioxane), ketones (such as acetone, methyl ethyl ketone, methyl isopropyl ketone and
  • Reaction variant (a) of the process according to the present invention is preferably carried out in the presence of acid acceptors.
  • Any of the customary acid-binding agents can be used as the acid acceptors.
  • Alkali metal carbonates and alcoholates such as sodium and potassium carbonate, sodium and potassium methylate or ethylate
  • aliphatic, aromatic or heterocyclic amines for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine, pyridine, diazabicyclooctane, diazabicyclononene and diazabicycloundecene
  • Reaction variant (b) of the process according to the invention is carried out in the presence of water and of one of the abovementioned organic solvents, provided that it is not miscible with water.
  • the abovementioned hydrocarbons are particularly suitable for this purpose.
  • the reaction temperature can be varied within a relatively wide range.
  • the reaction is carried out at a temperature between 0° and 100° C., preferably at a temperature between 10° and 50° C.
  • the process according to the invention is carried out, in general, under normal pressure.
  • the starting materials are customarily employed in equimolar quantities for carrying out the process according to the invention. An excess of either of the reaction components has no substantial advantages.
  • the starting materials are combined in suitable diluents and, if appropriate after the addition of an acid acceptor and/or a catalyst, are stirred until the end of the reaction.
  • the working-up can be carried out according to customary methods, for example by diluting the reaction mixture, if appropriate, with water and/or a water-immiscible organic solvent, such as toluene, separating off the organic phase, washing it with water, drying it and filtering it, and carefully distilling off the solvent from the filtrate, under reduced pressure and at a moderately elevated temperature ("incipient distillation").
  • a water-immiscible organic solvent such as toluene
  • the active compounds are well tolerated by plants, have a favorable level of toxicity to warm-blooded animals, and are suitable for combating arthropod pests, especially insects and arachnida, which are encountered in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene field. They are active against normally sensitive and resistant species and against all or some stages of development.
  • arthropod pests especially insects and arachnida, which are encountered in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene field. They are active against normally sensitive and resistant species and against all or some stages of development.
  • the abovementioned pests include:
  • Isopoda for example Oniscus asellus, Armadillidium vulgare and Porcellio scaber;
  • Chilopoda for example Geophilus carpophagus and Scutigera spec.
  • Symphyla from the class of the Symphyla, for example Scutigerella immaculata
  • Thysanura for example Lepisma saccharina
  • Orthoptera for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria;
  • Dermaptera for example Forficula auricularia
  • Anoplura for example Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.;
  • Thysanoptera for example Hercinothrips femoralis and Thrips tabaci;
  • Homoptera for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.;
  • Lepidoptera from the order of the Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta
  • Hymenoptera from the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.;
  • Siphonaptera for example Xenopsylla cheopis and Ceratophyllus spp.
  • Acarina for example Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp..
  • Acarus siro Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp.
  • the active compounds can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances and in coating compositions for seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans and fumigating coils, as well as ULV cold mist and warm mist formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances and in coating compositions for seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans and fumigating coils, as well as ULV cold mist and warm mist formulations.
  • formulations may be produced in known manner, for example by mixing the active compounds with extenders, that is to say liquid or liquefied gaseous or solid diluents or carriers, optionally with the use of surface-active agents, that is to say emulsifying agents and/or dispersing agents and/or foam-forming agents.
  • extenders that is to say liquid or liquefied gaseous or solid diluents or carriers
  • surface-active agents that is to say emulsifying agents and/or dispersing agents and/or foam-forming agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid diluents or carriers especially solvents
  • aromatic hydrocarbons such as xylene, toluene or alkyl naphthalenes
  • chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic or alicyclic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions
  • alcohols such as butanol or glycol as well as their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethylsulphoxide, as well as water.
  • liquefied gaseous diluents or carriers liquids which would be gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • ground synthetic minerals such as highly-dispersed silicic acid, alumina and silicates.
  • crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
  • non-ionic and anionic emulsifiers such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well as albumin hydrolysis products.
  • Dispersing agents include, for example, lignin sulphite waste liquors and methylcellulose.
  • Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations in general contain from 0.1 to 95 percent by weight of active compound, preferably from 0.5 to 90 percent by weight.
  • the active compounds according to the invention can be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, baits, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active compounds such as insecticides, baits, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons phenylureas and substances produced by microorganisms.
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergistic agents.
  • Synergistic agents are compounds which increase the action of the active compounds, without it being necessary for the synergistic agent added to be active itself.
  • the active compound content of the use forms prepared from the commercially available formulations can vary within wide limits.
  • the active compound concentration of the use forms can be from 0.0000001 to 100% by weight of active compound, preferably between 0.0001 and 1% by weight.
  • the active compounds When used against pests harmful to health and pests of stored products, the active compounds are distinguished by an excellent residual action on wood and clay as well as a good stability to alkali or limed substrates.
  • the active compounds according to the invention are also suitable for combating ectoparasites and endoparasites in the field of veterinary medicine.
  • the present invention also provides pesticidal composition containing as active ingredient a compound of the present invention in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.
  • the present invention also provides a method of combating pest (in particular arthropods, especially insects or acarids) which comprises applying to the pests, or to a habitat thereof, a compound of the present invention alone or in the form of a composition containing as active ingredient a compound of the present invention in admixture with a diluent or carrier.
  • a method of combating pest in particular arthropods, especially insects or acarids
  • the present invention also provides a method of freeing or protecting domesticated animals from parasites which comprises applying to said animals a compound according to the present invention, in admixture with a diluent or carrier.
  • the present invention further provides crops protected from damage by pests by being grown in areas in-which immediately prior to and/or during the time of the growing a compound of the present invention was applied alone or in admixture with a diluent or carrier.
  • the active compounds according to the invention may be used in a known manner in the veterinary sector, such as by oral administration, for example in the form of tablets, capsules, drinks and granules, by dermal application, for example by means of dipping, spraying, pouring on, spotting on, and dusting, and by parenteral administration, for example by means of an injection.
  • the toluene phase was then dried over sodium sulphate and the solvent was distilled off in a water jet vacuum.
  • the last solvent residues were removed by incipient distillation for a short time at a bath temperature of 60° C./1 mm Hg. 7.6 g (85.4% of theory) of (6-phenoxy-2-pyridinyl)-methyl ⁇ -isopropyl-4-trifluoromethyl-phenylacetate were obtained as a yellow viscous oil.
  • the structure was established by the 1 H-NMR.
  • Solvent 3 parts by weight of acetone.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether.
  • Cabbage leaves (Brassica oleracea) were treated by being dipped into the preparation of the active compound of the desired concentration and were infested with mustard beetle larvae (Phaedon cochleariae), as long as the leaves were still wet.
  • the destruction in % was determined. 100% meant that all the beetle larvae had been killed; 0% meant that none of the beetle larvae had been killed.
  • Solvent 3 parts by weight of acetone.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether.
  • Bean plants Phaseolus vulgaris which were heavily infested with the common spider mite or two-spotted spider mite (Tetranychus urticae) in all stages of development were treated by being dipped into the preparation of the active compound of the desired concentration.
  • the destruction in % was determined. 100% meant that all the spider mites had been killed; 0% meant that none of the spider mites had been killed.
  • Test insect Agrotis segetum larvae (in the soil).
  • Solvent 3 parts by weight of acetone.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether.
  • the preparation of active compound was intimately mixed with soil.
  • the soil was filled into pots and the pots were left to stand at room temperature.
  • test insects were introduced into the treated soil, and after a further 2 to 7 days the degree of effectiveness of the active compound was determined in % by counting the dead and live test insects. The degree of effectiveness was 100% if all the test insects had been killed and was 0% if just as many test insects were still alive as in the case of the untreated control.
  • Test insect Phorbia antiqua grubs (in the soil).
  • Solvent 3 parts by weight of acetone.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether.
  • the preparation of active compound was intimately mixed with soil.
  • the soil was filled into pots and the pots were left to stand at room temperature.
  • test insects were introduced into the treated soil, and after a further 2 to 7 days the degree of effectiveness of the active compound was determined in % by counting the dead and live test insects. The degree of effectiveness was 100% if all the test insects had been killed and was 0% if just as many test insects were still alive as in the case of the untreated control.
  • Solvent 35 parts by weight of ethylene glycol monomethyl ether; 35 parts by weight of nonylphenol polyglycol ether.
  • Emulsifier 35 parts by weight of ethylene glycol monomethyl ether

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
US06/355,044 1981-03-25 1982-03-05 Combating pests with novel phenoxypyridylmethyl esters Expired - Fee Related US4491585A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813111644 DE3111644A1 (de) 1981-03-25 1981-03-25 Phenoxypyridylmethylester, verfahren zu ihrer herstellung und ihre verwendung in schaedlingsbekaempfungsmitteln
DE3111644 1981-03-25

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US (1) US4491585A (fr)
EP (1) EP0061114B1 (fr)
JP (1) JPS57169461A (fr)
KR (1) KR880001864B1 (fr)
AU (1) AU548247B2 (fr)
BR (1) BR8201665A (fr)
CA (1) CA1162925A (fr)
DE (2) DE3111644A1 (fr)
DK (1) DK133982A (fr)
ES (1) ES8303344A1 (fr)
HU (1) HU188313B (fr)
IL (1) IL65311A (fr)
NZ (1) NZ200086A (fr)
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Cited By (2)

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Publication number Priority date Publication date Assignee Title
US4822806A (en) * 1984-01-12 1989-04-18 Ciba-Geigy Corporation α-methyl-(6-phenoxy)-2-picolyl cyclopropanecaraboxylates having pesticidal activity
US4920231A (en) * 1988-03-31 1990-04-24 Roussel Uclaf Process of braking triflouromethyl compounds

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Publication number Priority date Publication date Assignee Title
US4694013A (en) * 1985-11-08 1987-09-15 E. I. Du Pont De Nemours And Company Insecticidal and acaricidal phenoxypyrdinyl esters and intermediates

Citations (4)

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US4163787A (en) * 1977-03-14 1979-08-07 The Dow Chemical Company Substituted pyridine methyl esters of cyclopropane carboxylic acids and their use as insecticides
US4183942A (en) * 1976-08-27 1980-01-15 Fmc Corporation Insecticidal (β-phenyl-β-substituted-vinyl)cyclopropanecarboxylates
US4285954A (en) * 1980-11-19 1981-08-25 Zoecon Corporation Pesticidal S-pyridyl thioesters of phenylbutanoic acids and derivatives thereof
GB2079282A (en) * 1980-07-04 1982-01-20 Roussel Uclaf Parasitical carboylic acid esters containing a substituted pyridyl group

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JPS56147770A (en) * 1980-04-15 1981-11-16 Sumitomo Chem Co Ltd Novel carboxylic ester, its preparation and insecticide and acaricide containing the same as active constituent

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US4920231A (en) * 1988-03-31 1990-04-24 Roussel Uclaf Process of braking triflouromethyl compounds

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IL65311A (en) 1985-12-31
HU188313B (en) 1986-04-28
KR880001864B1 (ko) 1988-09-23
JPS57169461A (en) 1982-10-19
ES510752A0 (es) 1983-02-01
IL65311A0 (en) 1982-05-31
DK133982A (da) 1982-09-26
KR830009030A (ko) 1983-12-17
EP0061114B1 (fr) 1984-12-12
NZ200086A (en) 1984-11-09
BR8201665A (pt) 1983-02-16
CA1162925A (fr) 1984-02-28
AU8185282A (en) 1982-09-30
ZA821983B (en) 1983-02-23
AU548247B2 (en) 1985-12-05
EP0061114A1 (fr) 1982-09-29
ES8303344A1 (es) 1983-02-01
OA07046A (fr) 1983-12-31
DE3261501D1 (en) 1985-01-24
DE3111644A1 (de) 1982-10-07

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